


Don't Even Know Your Name

by frozensight



Category: Supernatural
Genre: Alternate Universe - Coffee Shops & Cafés, M/M
Language: English
Status: Completed
Published: 2012-04-13
Updated: 2012-04-24
Packaged: 2017-11-03 13:32:40
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 12,479
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/381859
Author URL: https://archiveofourown.org/users/frozensight/pseuds/frozensight
Summary: <blockquote class="userstuff">
              <p>Some Saturdays it paid off. He’d see them, and he would try his hardest not to outright stare as they passed. It was bad enough that he spent his Saturday mornings waiting for them to pass; he didn’t need to be <i>obvious</i> about it.</p>
            </blockquote>





	1. Chapter 1

Dean felt ridiculous, sitting at a table by the window of a coffee shop he barely even liked, waiting for someone who may not even come by that way ever again. And yet, every Saturday he found himself sitting at table by the large storefront window, sipping a mediocre cup of black coffee (sugar added only if he’d worked a late shift at work the night before), and he waited patiently from nine to ten before leaving. He spent an hour there, specifically that hour, every week, on Saturday, and waited for someone he didn’t know to pass by the window on their way to God knows.

Some Saturdays it paid off. He’d see them, and he would try his hardest not to outright stare as they passed. It was bad enough that he spent his Saturday mornings waiting for them to pass; he didn’t need to be _obvious_ about it.

It was somehow breathtaking each and every time Dean saw him (okay yes, it was a him, shut up). His hair was always disheveled, as if a comb was a foreign object or just something he never got the hang of using properly. Bright blue eyes were always focused, intent, on the sidewalk ahead of him, but Dean could tell that his mind was elsewhere. Another constant was the trenchcoat. Always the man wore this raggedy beige trenchcoat, whether there was a forecast of rain or not. The suit underneath may change, one day black and another grey, but the trenchcoat remained.

If Sam, his younger brother, had noticed that Dean had been leaving their apartment at the same time every Saturday morning, he had yet to say anything, and honestly Dean wasn’t sure what he’d say if Sam asked. “Oh yeah, I just go to this crappy coffee shop and wait for this guy to show up. No, I don’t know who he is and he doesn’t even come inside, he just walks past and I watch.”

Yeah, Dean was probably a certified stalker at this point, but he couldn’t bring himself to stop either.

October 6th started like any other Saturday. Dean got up at eight so that he could get ready and make it to the coffee shop before nine. He could only imagine his brother’s face if he knew that Dean drove twenty minutes every Saturday just to reach a coffee shop he didn’t even like, and that he had been doing it for almost two months now.

He parked in the back and walked around to the front of the coffee shop--Better Bitter. Like every other Saturday, he walked to the counter and ordered his drink, a medium, black coffee (not that there was much of a choice, which had been why Dean had tried out the place to begin with). The only difference this Saturday was the shop keeper, a creepy looking older guy, who if his nametag was correct was named Zachariah, spoke to Dean. And by spoke, Dean meant more than just him saying ‘hey here’s your coffee’.

“You know, Saturdays are probably the worst day to try and see him. He’s more likely to come by on weekdays.”

Dean stared blankly at Zachariah, his hand reaching out for his coffee automatically. “I...what?”

Zachariah smirked at Dean, handing over the coffee as he elaborated, “That guy you’re always waiting to pass by my window. He walks by basically every weekday--he even comes in sometimes, but hardly ever on Saturdays.”

Clutching the coffee cup like a lifeline even though it was fucking _hot_ , Dean continued to stare because this was not something he’d been expecting. He had never once ever imagined that the _coffee shop owner_ would call him out on his creepy habit (though in retrospect it did make sense). He couldn’t even form a single word to say to Zachariah because what was there to say when you’d been singled out as a stalker of a man whose name you didn’t know?

So he nodded--fucking _nodded_ \--and walked over to his usual spot by the window.

The man did not pass that morning, and Dean blushed when as he was leaving, Zachariah said loudly, “You should try coming on Mondays!”

~*~*~*~*~*~*~

Sunday was largely spent debating whether he should take Zachariah’s advice, or if that would just be taking his creepy to a whole new level. The inner battle rendered Dean to be in one of his less pleasant moods, and this did not escape Sam’s notice at all, especially when Dean glared at him for picking up the remote from the coffee table.

“Hey, I’m watching that!”

Sam gave his brother the most incredulous look Dean had seen in a while as he spared a glance for the TV before settling his gaze on Dean. “You were watching America’s Next Top Model?”

Eyebrows furrowed in confusion, Dean looked at the TV as an expression of disgust seemed to settle over his face in a grimace. It didn’t last long however, and he shifted in his place on the couch as he said, “Uh, yeah, I think Tyra’s choice of, uh, that girl was really smart because she sucked.”

Somehow, Sam’s face managed to express that his disbelief had deepened, if that was even possible at the moment, and Dean began to fear that an actual conversation involving _feelings_ might be in the near future. Those were his least favorite conversations to have with Sam because he always had to know everything Dean was feeling, and geez could a man have a little privacy?

“Dean, I think we both know that you do not watch America’s Next Top Model, and have never expressed an interest in doing so, _ever_.” Brown eyes locked with green, and yup Dean was definitely getting the dreaded vibe from Sam that meant he wanted to talk about emotions and other girly ass crap with him. Years of practice kept him from bolting out of their living room.

“People change, Sammy; for all you know, I’ve suddenly been wooed by Tyra’s charms.” The look on Sam’s face didn’t change--eyebrows remained raised in a way that typically came from a parental figure who knew you had taken the cookie from the cookie jar before dinner, but was going to wait until you admitted it before they punished you. Dean decided to go with his favorite course of action: play dumb. “What, Sam? Do I have something on my face?”

“Where have you been going every Saturday morning?” Well fuck, Sam zipped right past his act and jumped right in didn’t he? Not to mention that obviously Sam _had_ noticed his curious new habit, and had simply been waiting for the ‘right time’ to say something about it.

Unable to answer right away, Dean managed to keep up the eye contact until Sam’s stupid, big doe-eyes got too much and he had to look away. Fuck Sam and his ability to make Dean feel guilty for not telling him things, even small things like when they were out of toilet paper. The quiet lasted for almost a minute before Sam cleared his throat pointedly, making Dean sigh. Rubbing his face with his hands, Dean mumbled, “I’ve been going to this coffee shop.”

“I thought you hated coffee shops because they were always full of hipsters?”

“That’s because they are, but I like coffee so I sometimes put up with that particular evil.”

“So why Saturdays?”

Dean shifted a little again, this time more uneasily and he determinedly avoided Sam’s eyes. “I’m free Saturdays.”

“You’re free Sundays too, so why not go then?”

Thankfully, this answer was easy enough to avoid with actual truth, “It’s closed on Sundays.”

“Okay,” Dean allowed himself to relax a little, thinking Sam might settle for this and they could go back to watching TV (though hopefully not ANTM), but he should’ve known to expect his brother to be like a goddamn bloodhound, “So why do you spend a whole hour there if you’re just going for the coffee?”

“Um, well...” Shit. Dean’s right leg twitched, and he couldn’t help but sympathize with its desire to run away. “I really like their coffee?”

Cue Sam’s disbelieving bitchface. “Dean.”

“Sam.”

Sam heaved a sigh as if he was fighting the instinct to throttle him. “Can you please just tell me why you spend no more than an hour at this coffee shop every Saturday morning?”

Their eyes met again, and Dean saw that he was not escaping the couch without revealing his secret.

“Iwaitandwatchforthisguytowalkpastthewindow.”

Dean could tell from Sam’s startled face, that of all his half-formed predictions, that rush of words had not been one of them.

“You _what_?”

Eyes suddenly very interested in what Tyra said to the contestants, Dean repeated, “I-I wait and watch for this guy to walk past the window of the coffee shop, but he doesn’t appear every Saturday, so it’s like waiting for some random occurrence in a video game where you get some sort of special achievement for catching a rare monster or something, but every time it happens you’re way too afraid you’ll mess it up to do anything so you continue to sit and wait, hoping you’ll have the courage that next time you’ll say something to him, even though deep down you know you probably won’t, and--”

“Oh my God Dean you have a crush on a complete stranger.”

Oh how he wanted to punch Sam then, but he couldn’t because he was fucking right.

“Shut up.”

“You have a crush on a guy, and it’s actually turning you into a grade A stalker.”

“I said shut up, Sam.”

“Have you analyzed his clothing yet?”

“Wha--Sam who the fuck do you think I am? Some desperate teenage girl?”

Sam, by this point, was grinning so fucking widely that Dean was considering punching him anyway. “Oh my _God_ you have! Have you memorized his wardrobe yet? Or is it too early in the relationship for that?”

“Fuck off, Sam.”

Some of the amusement faded from his face, but Dean could still tell he was on the verge of laughter and that just made him even angrier and more embarrassed. “Dean, I’m sorry, but really, why haven’t you even tried talking to him?”

Dean snorted, a hand running through his hair in an attempt to calm himself, “It’s not like I can run out of the coffee shop and go up to him just to ask what his name is, that’s fucking weird, Sam.”

“And watching for him from a window for the past month or so isn’t?”

Having no way of answering that without entrapping himself further, Dean kept his mouth shut as he flipped open his phone, pretending he’d gotten a text from Jo or Victor. Sam huffed at the silence, and Dean swore he could _hear_ him roll his eyes.

“Dean, you have to try to talk to him or you’re just going to continue pinning for him, and I’m going to be the one who has to deal with your mopey ass.”

“Yeah, well when I become a psychic and can predict what days he’ll be walking by the coffee shop on Saturdays, I’ll let you know.”

“Considering you were spacing _before_ I tried to change the channel, I’m going to guess that there’s been some sort of new development that you’re not telling me.”

Dean looked at Sam, and he wanted to glare, he did, but Sam was doing his damn puppy face again and he couldn’t. “The shop owner may have called me out on my newly found coffee addiction, and suggested that I come by on weekdays.”

“Haha, even the owner noticed you?”

“Not helping, Sam.”

“Sorry, it’s just funny that you think the guy might not have noticed you if the _owner_ has found you out.”

If it was possible, Dean could have sworn that all color in his face fell away in that moment because _fuck_ what if sexy trenchcoat guy had noticed? What if he didn’t come by on Saturdays a lot because he knew Dean would be there in the window waiting and watching? Sam seemed to notice Dean’s drastic turn for the worse, and he grabbed his brother’s shoulder.

“Dean?”

“I can never go back there again.” His voice was soft, and he hated that it also sounded scared. He wasn’t used to being scared at the prospect of being rejected. That sort of phenomenon hadn’t happened since freshman year of college when Victor had turned down his advances, but at least then they’d remained friends. With Trenchcoat, that wouldn’t even be a possible notion.

“Oh come on, Dean. I’m sure it’s fine. I mean, if he has noticed, then he hasn’t said anything about it, to you or the shop owner. Maybe he likes you back?” He didn’t hesitate to glare at Sam that time. “Okay, perhaps a little presumptuous, but still, don’t give up when you haven’t even tried. That’s not like the Dean Winchester I grew up with.”

“Oh yeah?”

“Yeah, because the Dean Winchester I know wouldn’t have a second thought about going to that coffee shop tomorrow morning and talking to this mysterious window guy.”

“You’re not going to let this go are you?”

“I will escort you to this coffee shop tomorrow morning and stay with you until you at least get his name if I have to.”

Sam’s confidence in him was starting to have an effect, and he felt better just knowing his brother believed he could do this. He still felt dumb for the fact that it took a pep talk from his practically celibate little brother to get him determined for his mission, but beggars couldn’t be choosers.

“First of all, like _hell_ are you coming with me to the coffee shop tomorrow--I’m not even going to tell you what it’s called. Secondly, if he turns me away then it’s going to be you sporting the bill when we go to the bar tomorrow night.”

Smiling broadly, Sam chuckled, and it must’ve been infectious or something because Dean found himself sporting a small smile as well. “Deal, and he won’t turn you away.”

“Yeah, well we’ll find out tomorrow won’t we?”

~*~*~*~*~*~*~

Dean had barely taken a few steps into the Better Bitter before the urge to turn around and leave (and never come back) almost overwhelmed him. He had steeled himself for getting his coffee and then maybe waiting outside for Trenchcoat (it’s what he’d taken to calling the man in his head until he learned his name), but what he hadn’t anticipated was for Trenchcoat to already be inside when he got there.

Zachariah saw him right away when he entered, and grinned. Trenchcoat was at the counter ordering his coffee. Dean almost threw up right there because the proximity was making him nauseous. He didn’t want to approach anymore; he wanted to turn tail and run all the way back to his car. Yet somehow, the fact that he knew Sam would mock him for the rest of the year if he didn’t stay there and at least order something got Dean to hold his ground. Shakily, he walked up to the counter, standing just behind Trenchcoat to wait in line to order.

“Here you go: your usual medium with three sugars and cream.” Dean accidentally met Zachariah’s eye as he tried to get a better angle on Trenchcoat’s face, and the man winked at him, causing Dean to look away hurriedly, a blush forming quicker than he would like. He was so busy not looking that he almost ran into Trenchcoat as the man tried to walk away.

“S-Sorry!” Dean quickly stepped out of the way, hoping he didn’t cause Trenchcoat to spill coffee on himself or something.

Trenchcoat cocked his head slightly, his hand that held his coffee steady, blue eyes focused intently on Dean for the first time, and Dean was positive that much longer and he’d combust. “It is of no consequence. Perhaps you should be more attentive to avoid another such encounter. Have a good day.”

Dean would have stood there, stunned, for an hour or more if Zachariah hadn’t cleared his throat loudly once Trenchcoat had walked out the door and past the window. He jumped despite himself, whirling around to face a very smug Zachariah, who was already holding out a medium cup of coffee for him.

“Your order, sir.” Distinctly aware that his face was probably redder than it had been in forever, Dean slammed a five dollar bill on the counter and grabbed the coffee before stalking away. He could feel Zachariah’s eyes on him as he left, and probably a good portion of the other patrons were watching him too but he couldn’t bring himself to care.

Yes, he was embarrassed and frustrated and even a little pissed, but mostly? Mostly he was fucking ecstatic because finally after two months of just watching Trenchcoat from his chair by the window, _finally_ , he knew what his voice sounded like.

Naturally Sam made fun of him because he still didn’t have Trenchcoat’s real name, and Dean had accidentally called him Trenchcoat out loud when talking to his brother. Of course Sam’s response was, “Aww you have a nickname for him, how cute!” and Dean promptly punched Sam in the stomach before going to his bedroom to get changed for his shift at the garage.

Work, as always, calmed Dean down and helped him think. Sam had described it as like, cathartic or some other high class vocab word, one time and despite not knowing the exact meaning, it sounded like it fit. He enjoyed sliding underneath the various vehicles that came in, tinkering around with the valves and the gears in order to find out what was wrong, or just how to make the car function more efficiently. He was the newest employee at Singer Automotives, but it was no real secret that he was probably the best besides Bobby himself.

Dean wasn’t an ass about it though, he didn’t try to get any favors done for him, and worked just as hard as the rest of them. He usually volunteered to stay late on Fridays so that Jo could go on whatever date she usually had. He and Victor had bonded over childhood dreams that didn’t seem so easy once you graduated high school. Victor was working his way through his last year of college. He was due to graduate that spring with a major in criminal justice. Several times he’d tried to get Dean to re-enroll, but every time Dean would just shrug. He had to work. Law school was expensive, and Dean could finish college once Sam was safely nestled in at Harvard or some other big fancy schmancy Ivy League school. Until then, Dean was more than content to keep working at Singer’s, where the work was often hard, but fulfilling.

After the Close Encounters of the Trenchcoat Kind, Dean was incredibly grateful for the distraction that came in the form of 2009 Toyota Camry whose brakes were making a weird sound. It took him no time at all to discover that the main problem was just a couple loose bolts, but even after tightening them he examined the whole undercarriage just to make sure there wasn’t something else the driver should be worried about.

He was just pulling out from underneath when Victor walked up to him and with his hand gestured towards the office, and where the car’s owner was probably waiting for the final price. “Guy’s starting to get impatient, Winchester.”

Waving Victor off, Dean wiped his hands on a rag and made his way towards the office. He was in a good mood when he walked into the office to meet with the customer, a small grin playing on his face. Pushing the door open, Dean stuffed the rag in his back pocket as he walked over to the register and began punching in numbers. “Your problem was easy enough to fix, so I’d say your total should come to about $100.”

“Have we met before?” Dean looked up and his heart jumped because there before him stood Trenchcoat exactly as he had earlier that day, only the presence of his coffee cup was lacking.

Throat dry, Dean found himself temporarily unable to say anything. Why was this happening? He’d just wanted to slowly chat him up at the coffee shop, maybe eventually even find out his name, but not this, no this was too much. Finally he cleared his throat and said, “I-I kinda ran into you at Better Bitter this morning…”

Recognition dawned on Trenchcoat’s face, a tiny smile on his face that made Dean want to melt into a puddle and fuck he hated how girly this dumb crush was making him. It was probably Sam and his stupid feeling talks’ fault. “Ah, yes.” Trenchcoat met his eyes, and Dean found he was having trouble breathing as he stared back. The contact was broken when Trenchcoat reached around and pulled out his wallet. “$100, you said?”

Fumbling with the cash register for a second, Dean turned back to Trenchcoat and said, “I must’ve read it wrong, it’s only $75.”

Trenchcoat raised an eyebrow, and Dean hoped he wouldn’t question it. Bobby would probably already scold him for not charging full price, even though all he’d shaved off was just some of the labor fees—fees that’d directly affect Dean’s paycheck. It hadn’t really been hard work, so Dean didn’t want to charge Trenchcoat for something he’d had _fun_ doing. Thankfully, he just pulled out his credit card and handed it over.

It wasn’t how Dean had imagined, reading Trenchcoat’s real name off his credit card. He’d always thought he would learn it after charming him with his witty comebacks, or after buying him coffee.  Instead he was swiping Castiel Milton’s credit card through the cash register, and then handing it back with a small smile as the receipt printed.

“Castiel, huh?”

Letting out a sigh that spoke of just how many times this conversation has happened, Castiel stuck his wallet back into his pocket and replied, “My parents were rather sadistic in choosing some of their children’s names.”

Dean chuckled as he tore the customer’s receipt away from the store’s and held it out over the counter, “Well at least it isn’t Archibald.”

“My one saving grace.” Taking the receipt, Castiel nodded at Dean, turning away from him slightly. “Thanks for patching up my car; perhaps I will run into you at the coffee shop again.”

“Yeah, maybe…”

As he watched Castiel walk away, Dean couldn’t help but feel elated and embarrassed at the same time. For one, the tides had turned and Dean knew Trenchco— _Castiel’s_ name now and he didn’t know Dean’s, but on the other hand now he had to be less obvious about his coffee habits so it was more of a coincidence that they met again instead of purposefully stalker-like. He had made him smile at least, that had to count for something.

“Winchester! Get your ass back out here, there’s an Escalade out here with your name on it!” Bobby’s voice jarred him away from his thoughts, but nothing could make the bounce in his step from talking to Castiel— _Castiel_ —go away.

~*~*~*~*~*~*~

Dean didn’t go back to the coffee shop until Saturday. Sam told him he was acting childish, but Dean wasn’t going to push his luck. He’d worked up something of a routine, so it would be less weird if he happened to be sitting at Better Bitter and waved at Castiel from the inside than if he went Tuesday morning and bumped into him again.

So he waited.

By Wednesday, it was obvious that he was anxious about something. He’d accidently handed Victor the wrong wrench _twice_ , and he’d almost used the wrong brand when changing the oil of a Buick. Bobby let him go home early after Dean uttered a promise that he wouldn’t be so distracted the next day.

Waiting sucked, Dean decided about midday Thursday during his lunchbreak. It wasn’t fair that Sam had gotten most of the patience that their mom had seemed to possess because he could really use some at the moment. It was ridiculous how badly he wanted to talk to Castiel again, when he’d only talked to him for the first time a few days prior after _stalking_ him for months, but he knew it was necessary to play it cool. He didn’t want to come on too strong because shit he didn’t even know if Castiel would even be interested.

He almost went to Better Bitter Friday morning. He was about to turn into the parking lot when he saw Castiel’s Camry already there. Breathing heavily, Dean straightened out his car and drove to the nearest Starbucks. Funny though, he was so accustomed to Zachariah’s mediocre brew, that Starbucks actually didn’t taste quite as good.

Sam woke up before Dean left on Saturday morning and wished him good luck with a damn smirk on his face. He did the brotherly thing and flipped him the bird before slamming the front door of their apartment on his way out. The faint sound of laughter followed him, and Dean tried to think about ways to get back at his little brother instead of the fact his stomach was two steps from nauseous.

Castiel’s car wasn’t in the parking lot when Dean got there, but that wasn’t really a surprise considering Castiel didn’t even usually come to Better Bitter on Saturdays. A part of him was relieved that maybe he could get coffee like he usually did and pretend that maybe he and Castiel hadn’t talked and that he was still creepily watched for Castiel to pass. He was about to ponder about how weird it was that he could call him _Castiel_ now instead of Trenchcoat, which he was so used to that he was afraid that he might call him that out loud someday, that he didn’t realize it was his turn and that Zachariah was trying to get his attention.

“Sorry, I was…thinking.”

Zachariah snorted as he leaned on the counter and held out a small envelope between his forefingers, “I’m sure you were tiger. Here; it’s from you know who.”

Dean blinked, unsure, for a moment. You know who? He looked down at the envelope Zachariah was offering him, glancing for a second at the man’s face before taking it. Studying the lettering on the front, where he saw his name written in pen, Dean puzzled over who it was from. Zachariah seemed to think it obvious, if the way he was staring at him like he was an idiot was any indication. Then again, Zachariah always stared at him like that. He was about to ask who it was from when Zachariah shoved his usual coffee order at him.

“Ask who the letter is from, and I’ll make you pay for this.”

Shock still preventing him from speaking, Dean silently took the coffee as well, not sure what to make of Zachariah’s kindness. It felt a little like dealing with a demon. Turning slowly, he maneuvered around tables until he reached the one he had grown used to sitting at every week and sat down. He laid the letter down on the table in front of him, staring at it for a moment as he sipped his coffee, trying to figure out who it was from because if he assumed it was Castiel he was pretty sure his brain would malfunction.

After staring out the window for a bit around the time he could usually count on Castiel passing, Dean looked back at the letter. Setting down his coffee, he slowly picked it up and examined it again. The handwriting reminded Dean of how his tenth grade English teacher used to right on the chalkboard—neat and precise. Eventually he pried it open, taking out the letter inside and unfolding it. His jaw fell a little when he read it.

> _Dean,_
> 
> _I am disappointed that you didn’t try to come and “run into” me again on Tuesday morning, but I suppose that’s just how your strategy works. Anticipating the fact that you’re usually at Better Bitter on Saturdays, I am leaving this note with Zachariah today (Friday) because I will not be able to stop by myself as I am otherwise engaged. However, I would like to be the one to finally propose that we sit down and have coffee together for once; perhaps next Saturday as I know I will be free. I imagine it must be rather lonely sitting at that table in the corner by the window waiting for me to pass, so I think it will be rather nice to sit with you rather than walk past and pretend I don’t see you staring at me._
> 
> _If you would just leave your response with Zachariah, he will relay the message to me come Monday._
> 
> _Unless of course, you’d rather come and tell me yourself, that is also an option._
> 
> _-Castiel_

~*~*~*~*~*~*~

The rest of the weekend was spent freaking out over various things. Sam couldn’t seem to decide between his immense amusement at Dean’s panic or whether he should be concerned about how seriously Dean was taking a simple coffee date.

“Dean, you’ve gone on first dates before. I don’t get what the big deal is.”

“The big _deal_ Sam, is that this is Castiel we’re talking about, and I don’t want to screw this up.”

“Oh, you mean besides the fact he already knows you’ve been creeping on him for months?”

Dean wouldn’t give Sam the satisfaction of letting him see his older brother so flustered, so he locked himself up in his room for the rest of the weekend, leaving only when he knew Sam was out or asleep. Sam had knocked on his door at first, calling him childish, but Dean had just turned up the volume of his ACDC, Mrs. Weatherford downstairs be damned.

By Monday morning, his stomach felt like it was in knots partly due to nerves and partly because beer and hot pockets were only so filling. His body was heavy due to his inability to sleep well because all he could think about was Castiel and how he’d known Dean had been watching him for months and that he was apparently _fine_ with it and how he wanted to have fucking coffee with him. Dean Winchester was going on an honest to God _coffee date_ with the guy he’d been watching for two months. He couldn’t remember the last time he’d gone out for coffee with someone who wasn’t a just a friend or an old flame wanting to reminisce or rekindle.

When he had finished his coffee Saturday, he’d left a message with Zachariah containing his cell phone number and an affirmative just in case Plan A didn’t work. It wouldn’t work for sure if Dean didn’t hurry up and pick something from his oh-so vast collection of band shirts and solid color tees. What made it even worse was the fact that he could hear Sam in the kitchen getting ready for his own day and waiting for Dean.

He’d finally picked out the blue shirt he remembered several exes telling him looked good on him, and he was looking in the mirror for what probably was like the fifth time when Sam knocked on his door. “Dude, it’s 8:45; doesn’t it take like twenty minutes to get there?”

Tripping over his shoes as he tried to walk and put them on at the same time, Dean ended up hitting his head on his dresser. With one hand on his head, he opened the door to see Sam still standing there, looking far more impatient than he really had a right. His mouth made to open to issue a comment, but Dean held up a hand as he walked past to silence him. “Shove it, Sam. I don’t have time for this.”

He snagged his keys from the entryway table and left the apartment before Sam could try and give him some more advice he didn’t want.

~*~*~*~*~*~*~

After parking his car just as it turned nine, Dean all but ran inside Better Bitter. Panicked, he thought he’d missed Castiel, that his chance for Plan A—which was a better plan on all fronts—had come and gone. Zachariah whistled, drawing his attention to the counter, and then he pointed over towards the window where lo and behold, Castiel sat with his cup of coffee. He was reading a newspaper, and was so engrossed that he hadn’t noticed Dean’s entrance.

Smiling broadly, Dean walked up to Zachariah, occasionally looking over his shoulder at Castiel as if just to make sure he was still there. Rolling his eyes, Zachariah handed Dean his coffee, who faced the man and said, “He’s here—he’s still here.”

“I told him you wanted to give your answer in person, and he just sat down.” Zachariah took the money Dean handed him, and set about getting the proper change.

“Thank you.” Dean wasn’t sure what, exactly, he was thanking the odd coffee shop owner for, but it seemed the right thing to say.

“Whatever, just go over there and properly introduce yourself, dumbass,” grumbled Zachariah as he put some coins in Dean’s hand and waved him off.

Everything was suddenly very surreal. As he walked over to where Castiel sat, it felt like everyone was watching Dean’s every move, like everything was counting on this one moment. The closer he got, the more nervous he became because this was actually happening—he was actually going to sit down and talk with Castiel for longer than a minute. He wasn’t sure what he would do if it all turned out wrong, if Castiel ended up hating him and never wanted to talk to him again, or that this was actually all some sort of elaborate joke set up by Castiel and Zachariah, and that maybe Dean was actually about to get his heart crushed all over again and—

“Hello, Dean.” The words were simple, but they immediately pulled Dean out of his spiral of angst, his smile growing bright again just because Castiel was looking up at him.

“Hey, Castiel.”

Castiel smiled softly, glancing over at the chair across from him. “You know, you are allowed to sit down. This is, after all, your favorite table.”

Dean blushed as he sat down with his coffee because it was the table he’d always sat at on Saturdays, and Castiel seemed very proud of that fact that he knew exactly where it was. Fiddling with his cup for a moment, Dean mumbled, “So…about that coffee date…”

“Isn’t that what we’re doing right now?” Their eyes met, and Dean found himself falling into the deep blue that was Castiel. It made him grin wider than he had in a long time, probably since Sam’s high school graduation.

“I guess it is, isn’t it?”

Castiel laughed, and Dean loved the very sound of it—rich and yet soft. “I anticipated something like this could happen, and I have already made the personal commitment to not attend my first class of the day.”

His smile faltered, and Dean wasn’t sure why. Castiel had just skipped a class for him, he should be thrilled, and he was—but also he couldn’t shake the fact that he wasn’t really _convenient_ either. Noticing that shift, Castiel’s hand found Dean’s and squeezed it gently.

“There’s nothing to worry about, Dean. I’m just a student instructor for that class, and today was just a review day for the test on Wednesday. The students know how to contact me if they require my assistance.” He turned his head to the side, his smile taking up all of Dean’s immediate vision, and Dean couldn’t be bothered to look away. “I’m here because I want to be with you, don’t seem so eager to be rid of me when you’re the one who technically started this.”

Chuckling, almost self-deprecatingly, but Dean managed to reign it in a little, he replied, “Well, it’s not every day that the guy you’ve been watching calmly decides to have coffee with you.”

“Who says you were the only one doing the observing?”

That was a phrase Dean never thought he’d hear, and it did weird things to his stomach—not to mention his groin. “You were watching me?”

“It’s the natural reaction upon discovering you, yourself, are being watched, I would think.”

It was impossible to hold back the grin on his face because Castiel had been watching him. Dean wasn’t the only one utterly fascinated, and this somehow made everything better just knowing that Castiel was most definitely just as interested in Dean as he was in Castiel. The absurdity of this revelation—honestly, Sam would probably call him a dumbass when he relayed the conversation to him later—made Dean laugh, and he only laughed harder when he heard Castiel’s voice joining him.

The moment passed, but the mood remained. Dean gripped Castiel’s hand back so that their fingers intertwined, and they smiled at each other.

“People probably think we’re crazy,” commented Dean as he glanced around the coffee shop before his eyes landed on their hands, sitting in the middle of the table between them, looking so very natural that Dean began to wonder why he had taken so long to talk to Castiel in the first place.

“They haven’t spent the last couple of months working up the nerve to talk to a random stranger.”

It felt ridiculous and horribly cheesy, gazing into each other’s eyes like they were, holding hands and drinking coffee. Dean had the distinct feeling that they were re-enacting a scene from some chick flick, but he couldn’t find it within himself to give adman. They were perfectly content to just stare at each other, this time without a window between them.

“Is this the part where we exchange numbers, and promise to hopefully meet again?” asked Dean after a moment, his voice soft. He was afraid that speaking would ruin the moment, and that the moment would then be lost forever.

Castiel grinned. “No, this is the part where we exchange numbers and agree that you’re picking me up at seven on Friday night for our first real date.”

“Oh yeah? What are we doing?”

Dean’s eyes never left Castiel’s as the latter stood up, slipping a piece of paper into Dean’s hand as he did. “I don’t know, my date said it was a surprise.”

He fucking _winked_ as he walked out of the coffee shop, Dean staring shamelessly after him because this time he was actually allowed. He waited until Castiel passed the window until he looked at the piece of paper in his hand, smirking at the seven digits written there.

Suddenly, his watch went off and Dean realized that he was going to be late for work, and hurriedly added Castiel’s number into his contacts before darting out of Better Bitter and to his car. Not even Bobby yelling at him for arriving there thirty minutes late or the fact that he’d gotten grease all over what seemed like every inch of his body could wipe the smile off his face. When his shift ended, he waved cheerily to Jo and Victor, both of whom were shocked at his demeanor. In his car, he turned on his phone and saw he’d gotten several text messages. A couple of them were from Sam begging to know what had happened that morning, and there was a belated one from Jo telling him to get his ass to work. All the others were from one number, and just seeing the contact name on the screen of his phone made his smile that much brighter.

~*~*~*~*~*~*~

[from Trenchcoat @ 9:53 am]: I had a good time this morning.

[from Trenchcoat @ 10:02 am]: This class is incredibly dull.

[from Trenchcoat @ 10:05 am]: Why do you have to be working when I’m in class?

[from Trenchcoat @ 10:12 am]: Do you really not check your phone while you’re working? That’s unexpectedly proper of you.

[from Trenchcoat @ 10:19 am]: Have you given any further thought to what we’re doing on Friday?

[from Trenchcoat @ 10:30 am]: Sorry for bothering you while you’re working, I will stop.

[from Trenchcoat @ 10:38 am]: Is it weird for me to be missing you already?

[from Trenchcoat @ 10:39 am]: Right, I said I’d stop. I’ll just wait for your reply then.

~*~*~*~*~*~*~

[from Leatherjacket @ 4:36 pm]: this morning was awesome.

[from Leatherjacket @ 4:37 pm]: why would you purposefully take a boring class?

[from Leatherjacket @ 4:38 pm]: I only have  half-shift tomorrow.

[from Leatherjacket @ 4:38 pm]: I can entertain you now ;)

[from Leatherjacket @ 4:39 pm]: that was too forward wasn’t it fuck

[from Leatherjacket @ 4:40 pm]: sorry

[from Leatherjacket @ 4:40 pm]: you didn’t bother me

[from Leatherjacket @ 4:41 pm]: I miss you too don’t worry

[from Leatherjacket @ 4:42 pm]: sorry again for yeah…and sorry for not having my phone on me. I was late to work and didn’t want my boss even more pissed at me

~*~*~*~*~*~*~

[from Trenchcoat @ 4:43 pm]: You mentioned having a half-shift tomorrow?

~*~*~*~*~*~*~

[from Leatherjacket @ 4:43 pm]: yeah, I get off about 1

~*~*~*~*~*~*~

[from Trenchcoat @ 4:44 pm]: Would you like to get lunch?

~*~*~*~*~*~*~

[from Leatherjacket @ 4:45 pm]: you mean like a date before our date-date?

~*~*~*~*~*~*~

[from Trenchcoat @ 4:46 pm]: Think of it more like we’re slowly having each meal of the day together.

~*~*~*~*~*~*~

[from Leatherjacket @4:50 pm]: little restaurant down the street from Better Bitter?

~*~*~*~*~*~*~

[from Trenchcoat @ 4:51 pm]: Do not be tardy this time.

~*~*~*~*~*~*~

[from Leatherjacket @ 4:51 pm]: I wouldn’t dare.

~*~*~*~*~*~*~

Castiel looked at his phone fondly, smiling at the latest text from Dean even though he was in the library and technically phones weren’t supposed to even be on whilst inside, but no one ever followed that small stipulation.

“Finally got a response?” He met the amused face of his sister and current study partner for theology, Anna. He’d only just caught her up on everything that’d been happening at Better Bitter and how he was afraid he might have scared Dean off before they’d even managed a real date. She had told him to shut up and get back to memorizing all the Christian prophets for the test in a few days, and to stop worrying because he was at work for crying out loud.

“We’re having lunch tomorrow,” he told her happily. Anna smiled back at him.

“See? Nothing to worry about. Now help me come up with a mnemonic device for remembering all the major Christian denominations there are because there is far more than there should be.”

He set about creating a way to easily remember the twenty or so major denominations, but practically the whole time he was just thinking about how he was going to be seeing Dean again the next day, about how they would probably soon be officially dating, about how Dean wasn’t just that cute guy in the leather jacket sitting behind the window at Better Bitter watching him anymore.

**Notes for the Chapter:**

> Sorry if the texting part reads a little choppy, and there may be an epilogue coming, depending on what muses I get.


	2. Epilogue

“Dean what are you even worried about? Haven’t you already been on two dates with him?”

“Yeah, but this is a date-date, Sammy! He doesn’t even know where we’re going!”

Leaning against the wall outside of his older brother’s room, Sam looked towards the door, a small smile on his face as he asked, “Do _you_ even know where you two are going?”

There was some shuffling and something that sounded like Dean stubbing his toe on his bed or desk. “Of course I do, what am I some kind of idiot?!”

“Well…”

“Fuck off, Sam.”

“Hey, I’m just trying to help!”

“Well you’re not being very helpful!”

Rolling his eyes, Sam shifted so that he was facing the closed door—which was also locked, he tried that already—and said, “I could be of more help if I was actually allowed into your room, but you’ve banned me for some odd reason.”

“I don’t want you to see until I’m done.”

Sam laughed, “Are you doing that thing where it takes you three hours to get your hair _just right_?”

“It is not a thing.”

“You’ve done it at least ten times that I can think of excluding tonight—it’s a thing.”

The door suddenly swung open, and Dean stood there looking very disorganized and pitiful. His button-up was half on, Sam was pretty sure the t-shirt was inside-out, socks didn’t match, hair was in disarray, and wha—yup Dean’s fly was open too. The brothers’ eyes met, and Dean said sternly, “I need your help.”

Grinning because it was nice to see Dean freaking out over something that wasn’t a bill, work, or college tuition, Sam placed a hand on Dean’s shoulder and said, “All you had to do was ask.”

~*~*~*~*~*~*~

Castiel made sure to thank God again for sending Anna over before his date with Dean as his sister fussed with his hair and straightened his clothes. He’d been somewhere between panicking and calling Dean to cancel when she just appeared with her little smirk and a bottle of mousse.

“Let’s make this Winchester kid want to fuck you into next week,” had been her choice words of greeting, and Castiel had blubbered after her for a while because he and Dean hadn’t even _kissed_ yet, why was she aiming so high, Castiel just wanted to look nice, good even, not necessarily “fuckable”. Naturally Anna waved her hand at him dismissively as she looked through his closet when he voiced his concerns. “I meant it figuratively, like he’s going to _want_ to, but you’re not allowed to put out until at least the fifth date because you’re a Milton.”

“But why the fifth date?”

Anna had grinned at him as she pulled out one of his shirts and held it out to him. “Because it’s about the fifth date that you’ve been going out long enough to realize they’re probably committed to the relationship to some degree, and just early enough that you aren’t going crazy from wanting to jump them.”

Castiel didn’t have a good response to that, so she just took that as her cue to get busy.

Now they were at the phase of waiting for Dean to get there, having given him his address during lunch the other day. Anna made inquiries about what kind of car he drove, and all Castiel could say was, “It’s…black.”

She rolled her eyes at him as she patted his cheek. “Well, there’s one good topic for you to bring up in case things get awkward.”

“His car?” Castiel felt like that was cliché and personally kind of stupid. Anna just fixed him with a look that said ‘take my advice or I’m leaving you to wait by yourself and we both know you don’t want that’.

“If I’ve gathered correctly the kind of person this Dean Winchester is from what you’ve told me, then yes. He loves his car a lot, so talking about it will be something that he’ll happily do.” She made an amused snort as she walked away towards his kitchen. “I mean, doesn’t he work at a garage? Obviously he likes cars, come on Castiel—you’re double majoring, you should’ve been able to get that.”

Pouting the smallest bit, he followed his sister, “I just wasn’t sure if the job was because he enjoyed the work or because it was something he knew how to do.”

Anna nodded her head, giving him that, but she then turned and looked at him, “But still, he likes cars. Get him to talk about them, and I think you’ll have a hard time getting him to stop.”

Castiel almost told her that he wasn’t sure if he’d want him to stop, but she already had enough information to make fun of him for the rest of her life, he didn’t need to purposefully give her more. Instead he smiled at her and had opened his mouth to ask her what to do if Dean wanted to go back to his place, but then someone was knocking on the front door. Grinning widely at her brother, Anna made a mad dash towards the front door, only just beating him to it since he’d started running after her once he realized what she was trying to do.

“You must be Dean!” Anna greeted the man at the door cheerily, holding her hand out to him, which he took uncertainly. “I’m Anna Milton, Castiel’s sister.”

Relief seemed to spread over Dean’s face—or at least that’s what Castiel thought it looked like, Anna was currently trying to make him stay behind the door and he was attempting to push her away from it. “Oh, it’s nice to meet you, Anna. I’m Dean Winchester, but I’m sure you already knew that. Uh, where’s Cas?”

“Cas?” Anna looked at her brother behind the door, and Castiel stopped trying to shove her out of the way because he was blushing now. He hadn’t allowed anyone to call him ‘Cas’ since before high school, but when it’d slipped out of Dean’s mouth during lunch, he hadn’t the heart to tell him not to say it. For some reason, it sounded different when Dean said it. “Yeah, he’s right here.”

Before he could really comprehend what was going on, Castiel found himself facing dean, the door thrown wide open. Anna disappeared as if she hadn’t even been there, leaving Castiel to grope for words. “I, uh…hello, Dean.”

He was leaning against the doorframe, and Castiel couldn’t help but grin a little when he saw he was wearing his leather jacket. “You didn’t tell me that your sister lives with you.”

“She doesn’t. She showed up without my asking to help me get ready.”

Dean laughed lightly, and Castiel found himself smiling. “Yeah, I had a similar experience, except my brother waited outside my door until I let him in.”

They stood there, staring at each other, not realizing how much time was passing until from further inside the apartment, Anna yelled, “You two gonna stand there and make bedroom eyes at each other all night, or are you actually going to go on a date?”

Castiel blushed, quickly apologizing for his sister, before saying, “Just let me go get my coat.” When he came back wrapped in his trenchcoat, it was hard to ignore the distinct look of fondness in Dean’s eyes when he saw the coat. Tilting his head a little, Castiel stood in the doorway before Dean and asked, “What? Is there something on my face?”

“No, your face is fine—more than fine.” Then Dean held out his hand and waited until Castiel took it before he tugged it gently and added, “Come on, let’s get going.”

It took a lot of effort for Castiel to remember to shut the door behind him because the feel of Dean’s calloused hand on his was probably far more distracting than it should have been.

~*~*~*~*~*~*~

As seemed to be a norm when dealing with Castiel, Dean was incredibly nervous up until the point where he’s with him. It’s almost annoying how easily just holding Castiel’s hand makes Dean calm down. He’d been on the brink of panicking when he met his sister, but she didn’t seem to hate him so that was a plus. Since then he’d grabbed Castiel’s hand, instantly banishing all paranoid thoughts about how Castiel might not actually like him or that he’d think what Dean had planned was stupid.

He gazed up at Castiel, who was staring intently at his menu across the table. Dean had to stifle a laugh at how seriously he was taking his order because really, it was just cute. They were at Dean’s favorite burger joint, and practically the entire menu was comprised of burgers so Dean didn’t really understand why Castiel was having so much trouble choosing.

“Never had a burger before, or something?”

Castiel opened his mouth to answer, but after glancing up at Dean, he focused back at the menu, a small blush spreading over his cheeks as he meekly said, “…I have not had the pleasure, no.”

Dean almost fell out of the booth. “You’ve never had a _burger_ before?!”

“I am more inclined to sandwiches that are less likely to do me bodily harm.”

“Have you been talking to Sam or something, I swear—look, burgers now and then won’t do you ‘bodily harm’ or whatever.” Castiel still appeared unsure, so Dean took his hand, kissing his fingers before he was even thinking about it and said, “Hey, just try it; you may be surprised.”

There wasn’t much time for debate because their waitress chose then to show up. “Are you two ready to order now?”

“Yes, I’ll have the triple decker bacon burger, and he’ll have your classic cheeseburger.” The waitress nodded as she wrote it down before she left again. Looking back at Castiel, Dean saw the traces of a pout on his face, and leaned across the table a little to say softly, “Look, if you don’t like it, you can pick out dessert.”

“Even if it’s something you don’t like or have never had before?” Castiel was obviously challenging him, and Dean just smirked at him, glad that the slight pout was replaced with a playful grin.

“ _Especially_ if it’s something I don’t like or have never had before.”

“I will hold you to that, Dean Winchester.”

~*~*~*~*~*~*~

When their food finally arrived, interrupting the conversation they’d started about school, Castiel eyed his plate skeptically. He honestly wasn’t sure _why_ he’d never had a burger just that growing up Michael had never allowed it, so he’d become accustomed to not even wanting to try one. It did _smell_ good though, Castiel noted as he watched Dean take a huge bite out of his own ridiculously huge burger without pause. He observed Dean for a moment, thinking about how he also wanted a bite of _that_ , but apparently Miltons had to hold out for a while, something he clearly hadn’t been aware of when dating Balthazar or Crowley.

“You gonna try it, or just continue watching me eat?” Dean grinned at him, a tiny gob of mustard at the corner of his lips. Castiel almost reached over and thumbed it off without a word.

Instead he blushed a little because he’d been caught and picked up his burger. He stared it down for a moment before giving in and taking a hesitant bite. “Oh my,” he mumbled as he chewed slowly, savoring this new experience.

Dean laughed, renewing his attack on his burger. “Told ya they were awesome.” He winked and added, “And because I’m such an awesome guy, you can still choose dessert.”

At that point, Castiel nodded more out of reflex than anything because he was so involved in his burger that he hadn’t really registered what Dean had said.

~*~*~*~*~*~*~

After the success that was Castiel’s first burger, they went to eat dessert. When Dean had told Castiel that he could choose, he’d assumed that he would wind up having to eat one of the less favorable pie flavors offered there at the restaurant, however instead he found himself at a frozen yogurt shop, some place he’d normally make fun of Sam for visiting. He stared at all the flavors through glass with caution, Castiel walking along beside him with a soft smile on his face.

“But why would you _freeze_ yogurt?”

“It’s like eating ice cream, Dean.”

“Then why don’t we just get ice cream?”

“Because this is a healthier alternative.”

Frowning at the container of the proclaimed strawberry banana swirl, Dean grumbled, “Dessert isn’t supposed to be healthy.”

Castiel chuckled at him, which made Dean feel like he’d just won the lottery instead of the expected annoyance that he usually got when Sam laughed when he thought his older brother was being particularly childish.

Like Dean had ordered their burgers, Castiel casually walked up to the counter and ordered two small chocolate strawberry delights—whatever the hell that meant. Dean tried to pay for them, but Castiel frowned slightly and swatted his hands away when he made to pull his wallet out.

When the lady at the counter handed over the little cups of frozen yogurt, Dean took his and glared at it until Castiel said, “Keep glaring at it, and it’ll melt before you can even try it.”

Definitely not pouting, Dean gripped his spoon tightly and dug it into the surprisingly soft frozen dish. The spoon warily made its way into his mouth, and the moment the yogurt met his taste buds, Dean heard himself let out a soft moan. Castiel laughed again as he watched Dean hurriedly eat his cup before trying to steal some from Castiel as well.

~*~*~*~*~*~*~

“Come on, we have one more thing to do before you can go home,” said Dean as they got back into his car after they’d thrown away their trash.

“Oh?” Castiel hadn’t expected that. He had figured that after dessert Dean would take him back to his apartment and they’d kiss. If Anna was still there then she’d get kicked out, and rule about Miltons holding out be damned. Now though he was curious as to what else Dean could’ve possibly had planned.

The drive didn’t take very long, barely two songs had played completely before they pulled up to a building and Dean exclaimed, “Ta-da!”

Castiel leaned forward to see the neon sign on the front of the building, and he couldn’t help but smile widely when he read it. “A roller rink?”

“Yeah, I know, lame, but I thought it might be fun for nostalgia’s sake. You mentioned something at lunch about being liking skating when you were little, right? I mean, if you don’t wanna, we can go, it was just a stupid idea—”

“Shut up, or I’m leaving you in the car,” said Castiel as he unbuckled himself and opened the door before Dean could even reply.

~*~*~*~*~*~*~

Acquiring skates for two grown men was slightly embarrassing when you considered the fact that eighty percent of the rink’s patrons were younger than fifteen, but Castiel flashed Dean a bright smile and he found he couldn’t give  a single fuck.

“I haven’t gone skating in _years_ ,” commented Castiel as he laced up his skates with a practiced ease that Dean coveted.

“I haven’t been in a rink since Sammy was ten.” Dean finally finished lacing his and shakily stood up, trying just to stand straight and not even remind himself that he was supposed to _move_ in these damn things. Castiel got up with far more grace and Dean wanted to make a snarky remark, but Castiel was holding out his hand towards him.

“Well, let’s get our sea legs back together, shall we?” Melting into Castiel’s beaming face as he took his hand, Dean allowed himself to be led onto the rink, a small pit of dread forming in his stomach.

~*~*~*~*~*~*~

From the moment he’d seen Dean stand up in his skates, Castiel knew Dean had never actually skated in his life, or if anything never extensively. Amused and heartened by the fact that Dean would take him to a skating rink despite not being a skater himself, Castiel was gentle with him. He allowed them to hold hands, fingers eventually intertwining as they make their way around the rink in slow, wide laps. Or at least, he allowed it for a while before he grinned mischievously and let go of Dean’s hand.

“C-Castiel?” Dean’s voice hitched in fear, and Castiel supposed maybe he was being unnecessarily cruel, but really Dean looked so cute with his arms outstretched in an attempt to balance himself. He skated in a circle around Dean, hands tucked behind his back, making sure to stay just out of Dean’s reach, but alert for any sign that Dean might be falling. A frown was on Dean’s face, and Castiel told himself that laughing at him wouldn’t be very nice. “You skated more than just a little when you were a kid, didn’t you, you bastard?”

“Michael believed in having positive athletic outlets,” replied Castiel smoothly, skating off a little further and spinning in a tight circle before gliding back to Dean, who was struggling just to reach the wall.

“Well, yeah, and I played baseball in high school, but it doesn’t mean I could play a winning game after five years of no practice.”

Castiel skated closely to Dean, enough to whisper in his ear, “I also did gymnastics for a couple years.”

Dean fell almost immediately, right on his ass, and Castiel couldn’t help laughing that time as he continued to skate around him. Growling, Dean reached out when Castiel wasn’t paying attention and tugged on his shirt, causing him to lose balance and fall down next to Dean. Still laughing, Castiel leaned back on his hands and met Dean’s eyes, who had his arms crossed and was doing a bad job at looking mad.

“That was a dirty trick, Cas.” They were thankfully close enough to the wall that they were out of mostly everyone’s way and that Dean could use it to stand up again without falling again. Castiel got up without help, though very carefully.

“No, a dirty trick would’ve been telling you that my specialty had been the balance beam.”

He was awarded with the sight of Dean’s feet attempting to run away from him again. Laughing jovially, Castiel skated away from Dean, wanting to get in a lap or two himself before the DJ started one of the rink’s games.

~*~*~*~*~*~*~

Dean couldn’t even get annoyed at Castiel for ditching him to skate around the rink, leaving him to hang onto the wall. For one, Castiel looked so at ease as he skated, that Dean honestly wished he had just opted to stay on the sidelines to begin with so he didn’t have to worry about staying on his feet and could just watch Castiel move. Then again, clinging to the wall, slowly inching his way to an exit had its perks because Castiel would smile brightly and skate around him a couple times before shooting off again.

Yeah, definitely worth the undoubtedly large bruise currently forming somewhere on his ass.

Eventually Castiel stopped by Dean, holding out his hand again as the DJ announced that there was one last song until the race started. Grinning widely, Castiel said, “Come on, I promise I won’t let you fall.”

Giving him his most skeptical look since the frozen yogurt, Dean took his hand, definitely _not_ yelping when Castiel immediately took off.

He was essentially being dragged around in a giant circle, well oval, but Castiel’s hand was warm and comforting. Dean had just started actually moving his feet a little on his own when Castiel let go again. Panic began to set in when he felt two still very much warm hands on his hips.

“I promised not to let you fall, Dean,” whispered Castiel into Dean’s ear from behind. Dean stoutly ignored the way Castiel’s breath made him shiver and yet warmed him up at the same time, and instead tried to focus on _not falling_.

“This your sadistic way of giving me skating lessons, Cas?”

“No,” came his voice, honest as ever, “This is my selfish way of ensuring that the rink doesn’t get more of your ass tonight than me.”

If Castiel’s hands hadn’t been gripping him tightly to steady him, Dean knew he would’ve fallen again. Almost breathless at the mere thought that Castiel definitely wanted him that way, Dean said, “You gotta stop saying shit like that.”

“You’re right; there are children around.”

Taking Castiel to the skating rink was the best idea Sam had ever had, and Dean made the vow to thank him and do the dishes without complaint for a month.

~*~*~*~*~*~*~

It was with a small bit of reluctance that Castiel guided them off the rink as a bunch of the kids lined up for the race. Dean seemed incredibly relieved to be on carpet again, but he still made sure that Castiel didn’t let go of his hips until they had reached their shoes.

“I guess I know what I’m getting you for your birthday,” muttered Dean as he clumsily untied his skates and struggled to pull them off.

Castiel paused in tying his own shoes to gape at Dean. “My birthday?”

“Yeah,” continued Dean as if he hadn’t just implied that he expected them to be together long enough to exchange presents of any kind—and that was assuming they really were together now, “You should pick up skating again. It’s obviously something you’re good at and enjoy. Can you ice skate too?”

“Um, yes. I would ice skate during the winter and roller skate during the summer.”

“Makes sense.” Dean nodded as he fell silent, slipping his shoes back on before he grinned up at Castiel, “Hey, any chance you still have one of those tight as fuck outfits people always wear when ice skating, like on the Olympics?”

Returning the grin, Castiel answered, “I guess I know what to get you for your birthday.”

Dean bit back something that sounded an awful lot like a moan before he stood up and said, “We definitely need to go back to your place now.”

Taking Dean’s hand again as they walked up to the counter, handing over their skates, Castiel said bluntly, “I suppose I can also demonstrate the reason why I won several gymnastic competitions in high school.”

Despite the obnoxiously loud volume of the overused Cha Cha Slide song that was booming from any speaker that remained unbroken, Castiel still managed to hear Dean’s utterance of, “God help me.”

~*~*~*~*~*~*~

If Dean speeded a little on his way back to Castiel’s apartment, neither of them mentioned it. He wasn’t sure what exactly he was racing towards because he was fairly sure that Anna would still be there, she seemed the type to want all the details right after they happened, but he also got the sense that Castiel wanted this now as much as he did and didn’t think something like a nosy sister would stop him.

Parking shoddily by the curb, Dean only just managed to remember to feed the meter before jogging up the stairs to stand next to Castiel at the door to his apartment.

Their eyes locked. Dean wanted to ask if Castiel was sure, if he really wanted to do this now because Dean wanted to—oh man did he—but he was also scared that maybe they were going too fast, a notion that Dean hadn’t had in a very long time in regards to a relationship.

“I’m sure Anna won’t mind being kicked out of an apartment that isn’t even hers.” Castiel’s voice was calm, sure, and Dean relaxed because regardless of whether they had sex or not—regardless of whether they even _kissed_ —everything would be okay. He nodded, and Castiel opened the door.

“Hey!! Cassie’s back!” The voice that was unexpectedly _not_ Anna’s made Castiel halt only a couple feet inside his apartment, causing Dean to stumble into his back a little.

“Gabriel.” Peeking around Castiel, Dean glanced at his face to see that Castiel was not the same cheerful guy he’d been three seconds ago, and then followed the line of sight until he saw the man on the couch next to Anna in the living room.

“Gabriel?” asked Dean quietly, unsure if he should just leave and text Castiel later.

Castiel let out a long sigh, and opened his mouth like he was about to explain, but the man in question beat him too it by jumping up from his seat and walking over to them. He was shorter than Dean had expected, and stared at the outstretched hand for a moment longer than necessary before shaking it. “Gabriel Milton, big bro to little Cassie here.”

“I thought Michael was your older brother?” Dean looked to Castiel, confused and mildly uncomfortable because Gabriel wasn’t letting go of his hand for some reason.

“Michael is the eldest of the four of us,” ground out Castiel, his blue eyes intent on trying to burn a hole in Gabriel’s skull. Dean had a feeling that he would be unsuccessful.

“And Michael’s also a giant party pooper because he refused to come to Milton family night!” Gabriel finally let go of Dean’s hand to walk back to the living room and stand with his arms in the air as if he was displaying the puzzle in Wheel of Fortune. On the couch, Anna was grinning smugly, and Dean had the distinct impression that some sort of intervention was being had.

“He probably declined because there is no such _thing_ as Milton family night.” Castiel’s voice was low and threatening, and it was a conscious effort by Dean not to cower behind him and just let the sibling battle happen.

“That’s why we’re starting it!” Anna stepped forward, hands behind her back as she stood next to Gabriel, a coy look still on her face.

Castiel actually growled.

“L-Look, I can go, and I’ll just call you later or somethi—”

Dean got cut off when one of Castiel’s hands grabbed his left shoulder and held him still so that escape was impossible. “You aren’t going anywhere, Dean Winchester.”

Gabriel shrugged, “Sorry bro, only Miltons at family night.”

“Well Dean and I aren’t going to be _attending_ family night because it isn’t happening, and even if it was, it wouldn’t be happening in my living room.”

“Awww, Cassie, but we already ordered a pizza!” It was a miracle that Castiel hadn’t exploded yet because Dean knew if Sam had done something like this he would’ve been yelling and punching by now.

Closing his eyes and steadying his breath, Castiel gripped Dean’s shoulder more tightly for a moment. “Let’s go outside, Dean.”

“O-Okay.” It wasn’t like Dean had a choice because Castiel was dragging him along in his journey back through the door. He waved weakly over his shoulder at Gabriel and Anna. “It was nice to meet you, I guess.”

“Remember the Milton rule, Cassie!” were the last words heard from them as the door closed behind Dean and Castiel for the second time that night.

Eyebrow raised, Dean looked at Castiel and asked, “What’s the Milton rule?”

The glare he got from Castiel was expected, Dean had long since realized he was being cockblocked by Castiel’s older siblings, but the kiss wholly surprised him.

He didn’t object to being pushed back against the wall next to the door. Or the fact that one of Castiel’s hands was cupping his face while the other held tightly to his waist. The kiss was rough and obviously anger induced, and Dean couldn’t help but push back and try to get as much as Castiel as he could. He’d been wanting to kiss Castiel for more than two months; Dean can’t remember a time he was more patient.

“Sorry about them,” was the first thing Castiel said when he pulled away, his forehead resting on Dean’s, eyes downcast. “They seem to desire to uphold a frivolous familial rule that proclaims we have to wait until the fifth date until we initiate intercourse, which is preposterous because they’ve never mentioned it prior to today.”

“It’s okay, really.” Dean leaned forward just enough to touch noses with Castiel and place a chaste kiss to his lips. “Really, it’s fine. I know Sam would do something similar if he thought I wouldn’t beat him up.”

Castiel chuckled, eyes lazily rising to meet Dean’s. They didn’t speak for a while, far more content with just staring at each other, with breathing the same air, with just being. Eventually though, Castiel’s phone went off to the tune of [insert an obnoxious song] and he groaned in annoyance before he took it out of his pocket and answered, “Fuck off Gabriel,” and then hung up.

A couple seconds passed and then Castiel’s phone beeped and the text from Gabriel just read: “ _rude_ ”. Dean laughed and Castiel just snorted before shutting his phone angrily and stuffing it back in his pants’ pocket.

“Next time,” Castiel began as he pressed the rest of his body against Dean, as if he was trying to collapse on top of him, “ _Next time_ , we are going to your place.”

“You know I have a sibling too, right?” Dean teased, already knowing he could easily make Sam leave the apartment whenever he wanted.

“If I want Sam to vacate the apartment, he _will_ vacate the apartment.”

Dean laughed lightly before kissing Castiel again, this time more slowly and more tenderly, like he wanted to have this to cherish for a couple days, which he did and he’d have felt girly about it but he got the feeling Castiel felt the same way. They didn’t part for a couple minutes, neither one feeling up to saying goodbye, not when they felt like their evening got cut short.

The decision was made for them when Anna opened the door and smirked at them, “Come on, Cas, you don’t want the pizza man to find you like this do you?”

Castiel glared at his sister until she just winked at them and went back into the apartment. He turned to Dean, kissed his forehead, and said, “Call me in a couple hours.”

He then entered his apartment with only one last meaningful look at Dean before they were separated. Dean stayed there, leaning against the wall for a while until he heard what sounded an awful lot like a pizza guy and figured that was one position he didn’t want to be caught in by some fifteen year old. Ruffling himself up, Dean made his way back down the stairs to his car, nodding at the pizza guy as they passed each other.

When he got to his car, he just sat in the driver’s seat for a couple minutes before it fully hit him that it was a Friday night, he wasn’t having sex with his date, and that he was _happy_ about the way the night had gone in spite of that. Because really, if the sex was even going to marginally reflect how kissing Castiel had felt, Dean felt that it would be well worth the wait.

Grinning to himself, Dean started up his car and began the drive back to his apartment, not sure when he’d be seeing Castiel again, but knowing it wouldn’t be soon enough.


End file.
